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para ‐Quinone Methides as Acceptors in 1,6‐Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules
Author(s) -
Lima Carolina G. S.,
Pauli Fernanda P.,
Costa Dora C. S.,
de Souza Acácio S.,
Forezi Luana S. M.,
Ferreira Vitor F.,
Carvalho da Silva Fernando
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901796
Subject(s) - chemistry , nucleophile , electrophile , nucleophilic addition , conjugate , molecule , reactivity (psychology) , quinone , combinatorial chemistry , addition reaction , context (archaeology) , photoredox catalysis , catalysis , stereochemistry , organic chemistry , mathematical analysis , mathematics , medicine , paleontology , alternative medicine , pathology , photocatalysis , biology
para ‐Quinone methides ( p ‐QMs) are naturally occurring molecules that have been finding increasing synthetic applications in the last few years. The presence of two electronically different exocyclic conjugate substituents in their structure, carbonyl and methylidene, leads to a pronounced reactivity owing to the polarization of the molecule. In this sense, those are prone to undergo the attack of nucleophiles in the terminal carbon exocyclic double bond, behaving as vinylogous electrophiles and generating 1,6‐addition products. In this context, in the last few years the development of catalytic approaches for 1,6‐nucleophilic addition reactions involving p ‐QMs has attracted considerable attention. Considering the extensive applications that such molecules have found in the last decades in 1,6‐addition reactions, in this review we comprehensively discuss the historical development of this field, starting with early approaches on natural product synthesis, going through seminal non‐stereoselective processes and progressing to cutting‐edge asymmetric‐catalyzed approaches.